Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate

Hamon, Nadege, Quintiliani, Maurizio, Balzarini, Jan and McGuigan, Christopher ORCID: https://orcid.org/0000-0001-8409-710X 2013. Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate. Biorganic and Medicinal Chemistry Letters 23 (9) , pp. 2555-2559. 10.1016/j.bmcl.2013.02.117

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Abstract

We report in this Letter the synthesis of prodrugs of 2-fluoro-2-deoxyarabinose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate. We demonstrate the difficulty of realising a phosphorylation step on the anomeric position of 2-deoxyribose, and we discover that introduction of fluorine atoms on the 2 position of 2-deoxyribose enables the phosphorylation step: in fact, the stability of the prodrugs increases with the degree of 2-fluorination. Stability studies of produgs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate in acidic and neutral conditions were conducted to confirm our observation. Biological evaluation of prodrugs of 2,2-difluoro-2-deoxyribose-1-phosphate for antiviral and cytotoxic activity is reported.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Optometry and Vision Sciences Schools > Pharmacy Research Institutes & Centres > Systems Immunity Research Institute (SIURI)
Subjects:	R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords:	Sugars; Deoxyribose; Phosphorylation; Prodrugs; Fluorination
Publisher:	Elsevier
ISSN:	0960-894X
Last Modified:	25 Oct 2022 08:27
URI:	https://orca.cardiff.ac.uk/id/eprint/53045

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